writing about handing power back to educators and families – and other thoughts

Advice for Ambitious 19 Year Olds Who Want to Work in Education

I just read Sam Altman’s blog post on career advice for the start-up industry. I enjoyed his post.

Here’s my version for the education sector. Of course, the world (thankfully) is not so ordered that you can plot your way to changing the world. But you can (and should) put yourself in situations that increase the probability that you can change the world (if that is your ambition, which it need not be).

Lastly, I know some folks think posts like this are obnoxious. But I wish adults had been honest and open with me about this stuff when I was nineteen. No one was. This caused me to make some early mistakes that I regret in that they decreased meaning, happiness, and purpose.

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1. Go to a College that Offers Rigorous Coursework and Great Classmates – and Don’t Solely Major in Education

If you want to impact education, it’s best that you go to college, as education is a fairly regulated industry that often requires a degree of some sort, especially to teach. Unfortunately, in too many schools education coursework is not rigorous. So you should major in something rigorous that ideally aligns to your emerging strengths and includes some quantitative coursework; good matchings include: policy and systems strength (economics); quantitative and logic strengths (engineering, computer science); writing strength (philosophy, history). While in college, you should find ways to get real world experience in leadership and working in teams. You should get to know a lot of awesome people; maybe even do some drugs. For all of these reasons, you should go to a college where you are confident you can get rigorous coursework and meet great people. Such schools come in all shapes, sizes, and prices.

2. Teach or Become a High Dosage Tutor at a High-Performing School

You don’t have to have worked in a classroom to affect education; however, not teaching will limit your opportunities down the road and will risk creating instructional blindspots that can be difficult to overcome. If you simply aren’t built for teaching a full classroom of students, do full-time high dosage tutoring. Either way, join up with a high-performing school. It might feel good to be a martyr at a terrible school, but you will not change much and you will have lost two years where you could have been building the skills that would allow you to really help children over the long-haul. At minimum, teach for as long as it takes you to become pretty good (most likely at least three years) or as long as it takes to realize you will never be good at it (most likely at least two years).

3. Start Taking Small Bets and Learn From Them

On your way to becoming a good teacher (probably in year two or three) start taking small bets that align with your passions and emerging strengths. Grab some coworkers and create an education app. Volunteer at a think tank. Create a new class at your school. Spend the summer working in a developing nation. Start a blog. Work on a political campaign. While you are making these small bets, make sure you’re listening to the feedback. What do you enjoy? What are you better at than other people? In the future, what might you be better at than most people? In the future, what might you be better at than 99% of people? What might actually help kids? What might not?

4. Then Take a Big Bet with a Great Team Where You Will Grow 100x

At some point, take a big bet. This could be in teaching: you could attempt to team up with some great math educators create the world’s best high school Geometry curriculum. It could be in entrepreneurship and leadership: you could join the founding team of a very innovative or high-growth charter school. It could be in ed tech: you could join a start-up or early stage company. It could be in a union: you could partner with likeminded educators and launch a new union. Ideally, you’ll want to join a smallish team that is led by a few amazing people who can challenge you immensely and from whom you can learn a ton. If you launch something yourself, you’ll likely be trading deep mentorship for ownership, so make sure you get some great informal or formal advisors. Also, whatever you choose to do should have an incredibly high upside – if it works, does it have a chance to change the game for kids?

In most cases, don’t set your eyes on trying to move up in a larger organization. While you can do a lot of good by contributing to a large organization, in most cases you won’t get the experiences you need to grow 100x. Starting new entrepreneurial ventures within a large organization (if they let you) might be an exception (but probably not).

5. Continue Doubling Down on High Upside Opportunities that Align with Your Strengths

At some point you should figure out what you’re really good at it (you generally have to be really good at something if you want to change the game for kids). Then keep taking opportunities that utilize these strengths and have high upsides for kids. If you get in a rut, go to grad school. If you’re not in a rut, don’t go to grad school.

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Just some thoughts. Again, life is not so easily planned, but the above are things to consider.

As for me:

I did (1) poorly: I majored in English at Tulane which turned out not be rigorous. It wasn’t until law school that I was pushed to be a more rigorous thinker.

I did (2) poorly: I did not teach, which I regret.

I did (3) well: While in law school I worked and lived in Sierra Leone; worked in India; wrote a novel; led a legal team on an education lawsuit; volunteered in New Orleans after Katrina. I made a lot of small bets.

I did (4) well: I teamed up with Sarah Usdin and Matt Candler to launch New Schools for New Orleans. I grew 100x and eventually became CEO. I think we did a lot of good for kids.

1: There are a couple degree programs more rigorous than physics at Carnegie-Mellon. But just a couple. Score. Followed up with MBA work at U Illinois Champaign, with a does of artificial intelligence, machine learning, and foreign policy. Score. Never have touched drugs, and with the downside am amazed you would recommend it. No score.

2: Haven’t taught more than a few hours. On the other hand, I have also never flown a military aircraft, but I successfully redesigned one of those. Thanks to modern technology and society, have spent many, many hours with teachers. Hopefully their cumulative experience will guide me. Rather than a more limited personal experience with all the scars that come there. No score on your scale; I’ll take my experiences.

3: Yep, Including time with teens in juvenile court and in volunteer settings. Score.